22 Things to Do in Pittsburgh This Week · June 18–21, 2026

Festivals & Special Events

Juneteenth Boat Party on the Gateway Clipper

An all-Black boat party on the Gateway Clipper celebrating Juneteenth on Pittsburgh's rivers.

Thursday, June 18, 2026 · Gateway Clipper, South Shore

WPA Juneteenth Celebration at Point State Park

Western Pennsylvania's official Juneteenth celebration at Point State Park with live events and community festivities.

Friday, June 19, 2026 · Point State Park, Downtown

Millvale Pride Drag Brunch at Strange Roots

Celebrate Millvale Pride Day with a fierce drag brunch at Strange Roots Experimental Ales in Millvale.

Saturday, June 20, 2026 · Strange Roots Experimental Ales, Millvale, PA

Squirrel Hill Night Market

Massive night market on Murray Ave featuring 100+ local artists, small businesses, live music, food trucks, and community festivities, 6–10 PM.

Saturday, June 27, 2026 6:00 PM · 1839 Murray Ave, Pittsburgh (Squirrel Hill)

Arts & Culture

One Mo' Gain: 30 Years of Cave Canem

A free poetry and visual arts event at the August Wilson Cultural Center celebrating 30 years of Cave Canem.

Thursday, June 18, 2026 · August Wilson Cultural Center, Downtown

Outdoors & Active

Blacksmithing Basics at Carrie Blast Furnaces

Learn hands-on blacksmithing basics at the historic Carrie Blast Furnaces in Rankin.

Thursday, June 18, 2026 · Carrie Blast Furnaces, Rankin

City of Bridges Run Club – Monday Oval Workout

Coach Kim leads a weekly evening track workout at Schenley Oval — open to all runners.

Monday, June 22, 2026 · Schenley Oval, Pittsburgh

Schenley Park Fest

A casual park day with food trucks, lawn games, picnic blankets, and community fun at Schenley Park Overlook, 3–6 PM.

Saturday, June 27, 2026 3:00 PM · Schenley Park Overlook, Pittsburgh

Music & Nightlife

Savannah Dexter at Jergels Rhythm Grille

Country artist Savannah Dexter performs live at Jergels Rhythm Grille tonight.

Thursday, June 18, 2026 · Jergels Rhythm Grille, Warrendale

Drag Bingo at Eleventh Hour Brewing

Pride Drag Bingo night at Eleventh Hour Brewing with six games of bingo and a fabulous drag show, bingo kicks off around 7 PM.

Saturday, June 20, 2026 7:00 PM · Eleventh Hour Brewing, Pittsburgh

Passion Pit – The Pretty Penny Tour

Passion Pit brings their indie-pop sound to Stage AE indoors on Monday night with support from Arden Jones, presented by 91.3 WYEP.

Monday, June 22, 2026 7:00 PM · Stage AE, Pittsburgh

Brake Run Album Release w/ Sgt. Hare Apollo and A Cute Angel

Local shoegazers Brake Run celebrate their new album at The Government Center with Columbus alt-rockers and sweet openers.

Thursday, June 25, 2026 8:00 PM · The Government Center, Pittsburgh

An Evening With Joe Grushecky and the Houserockers

Pittsburgh rock legend Joe Grushecky and the Houserockers take the intimate City Winery stage for a special evening.

Friday, June 26, 2026 · City Winery Pittsburgh, Strip District

Free Events

Juneteenth in the Square – Market Square

Free Juneteenth community celebration in Market Square with live programming and vendors running through June 21.

Friday, June 19, 2026 · Market Square, Downtown

Dance & Fitness Classes with Pittsburgh Ballet Theatre

Free outdoor dance and fitness classes with Pittsburgh Ballet Theatre at Arts Landing, running Saturdays through September.

Saturday, June 20, 2026 · Arts Landing, Pittsburgh Cultural District

Kendra Gives Back Shopping Event

In-store shopping event at Kendra Scott in Shadyside with light sips and sweets; 20% of purchases benefit Open Up Pittsburgh.

Saturday, June 20, 2026 1:00 PM · Kendra Scott, Shadyside

Free Concert at Hazelwood Green – Son Rompepera & El Montenegro

Free outdoor concert at Hazelwood Green featuring Son Rompepera, El Montenegro, and special guests, with food trucks and breweries, all ages.

Sunday, June 21, 2026 · Hazelwood Green, Pittsburgh

Food & Drink

Disco Drag Brunch at Velum Fermentation

A disco Pride Month drag brunch with performances, doors at 11 AM and showtime at noon, at Velum Fermentation in the South Side.

Saturday, June 20, 2026 11:00 AM · Velum Fermentation, 2120 Jane St, Pittsburgh

Family-Friendly

Cinema in the Park – 'Creed' at Grandview Park

Free outdoor screening of 'Creed' (PG-13) at Grandview Park Bandstand as part of Dollar Bank Cinema in the Park.

Saturday, June 20, 2026 · Grandview Park Bandstand, Pittsburgh

I Made It! Market at The Waterfront

Outdoor artisan market featuring over 35 local artists and food vendors at The Waterfront in Homestead.

Saturday, June 20, 2026 11:00 AM · 100 West Bridge Street, West Homestead

Date Night

Summer Alfresco Wine Dinners at The Priory Hotel

Intimate outdoor wine dinners under the stars featuring four Spanish wines paired with four chef-crafted tapas and live music at The Priory Hotel.

Friday, June 19, 2026 · The Priory Hotel, Pittsburgh

Pittsburgh SUMMER LOCK & KEY SINGLES PARTY

A fun singles mixer at Ruckus Cafe where guests exchange lock and key charms to meet new people, ages 29–59.

Saturday, June 27, 2026 7:00 PM · Ruckus Cafe, Pittsburgh